2,4,6-Trichlorophenyl isothiocyanate → Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(2,4,6-trichlorophenyl)carbamothioyl]amino}benzoate

HRID 1398911Notes

Reaction equation

HRID 1398911 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[C:20]=1[N:27]=[C:28]=[S:29]>>[Cl:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[C:2]=1[NH:1][C:28](=[S:29])[NH:27][C:20]1[C:21]([Cl:26])=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[Cl:18]

Participants

3

Reactant 2

HCID 1233992,4,6-Trichlorophenyl isothiocyanateHCID 68739849Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate

Product 1

HCID 86632911Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(2,4,6-trichlorophenyl)carbamothioyl]amino}benzoateYield 74.3%

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (200 mg, 0.773 mmol) and 2,4,6-trichlorophenyl isothiocyanate (406 mg, 1.70 mmol) was stirred at room temperature for 2 days and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture to give the title compound as a red oil (285 mg, 0.574 mmol, 74%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-0d4b36ab468f45d9a6b7dc66e846629a
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…